There have been two infamous “beer summits’ during the Obama administration. First, there was drinks with Harvard professor Henry Louis Gates and the Cambridge police officer who arrested him on his porch, to calm rising racial tensions.

Then there there was the first meeting over drinks between the president and House Speaker John Boehner.

Yet neither have anything on the “Cosmo Compromise” that may never take place, seeing as Cosmopolitans, the drink of choice for Congresswoman Maxine Waters, is a cocktail the White House may not be interested in mixing.

Rep. Waters has been one of the most vocal agitators of the president over that last few months, stemming from comments made during an August CBC jobs town hall meeting in Detroit. Since then, the Congresswoman has consistently challenged the president to specifically address the double digit African-American unemployment crisis with targeted strategies and support for black communities.

During the 42nd Annual Congressional Black Caucus Legislative Conference Dinner last week, the president delivered a rousing speech. A speech that had many in the audience previously — even currently — frustrated with some of the perceived disconnection of the White House with black constituents, charged and prepared to reengage, with a fervor that had dissipated over the past few months.

As the president concluded his message, he gave a charge that some in the audience and around the country took issue with when he said, “I expect all of you to march with me and press on. Take off your bedroom slippers, put on your marching shoes. Shake it off. Stop complaining, stop grumbling, and stop crying. We are going to press on. We’ve got work to do, CBC.”

These comments gave way, opening a space for Waters to ask to whom was the president speaking. She and others, including Cornel West (who has been even more critical of the president) made separate comments that the president would never speak that way to the Jewish community or the business community. Waters went on the Sunday morning news show circuit and reminded the president that she and others, “challenged Presidents Reagan, both Bushes, and Clinton on policy issues related to the African-American community, and that he should be no different. ”

The president even to some degree acknowledged the validity of the Congresswoman’s argument during a recent interview with BET News.

“There have been a handful of African-American leaders who have been critical,” Obama told BET News. “They were critical when I was running for president. There’s always going to be somebody who is critical of the president of the United States. That’s my job.”

“Particularly, when the economy is going as badly, as it is right now, people are going to have concerns. And they should,” he added.

But the challenge with this back and forth is for whom does it really serve? While many on the left have been frustrated that the president has not been more aggressive regarding core “progressive” values. Most people in the African-American community are not stereotypical liberals, yet they remain optimistic about “hope and change.” The president’s policies have, for the most part been in line with traditional civil rights and black faith ideology.

Truthfully, the administration has not been aggressive in messaging around black and poor people’s issues. Furthermore, the administration has not been affective in messaging the legislative successes and executive mandates they have championed and their impact on members of the black community (and other Americans) who are unemployed, underemployed, uninsured and living in poverty.

Even Waters’ own words have become terribly personality versus policy driven. In spite of that, if President Obama is to regain the White House that message needs to be crystal clear.

While a one-on-one meeting between President Obama and Waters may create an alliance that could be more beneficial during the general election than the White House might be willing to admit, there is a larger concern. That concern is whether or not the “Cosmo Compromise” takes place, those that support the re-election bid of the president must make the discussion larger than one Congresswoman versus the president.

There is an African-American contingency represented by the likes of Cornel West and Tavis Smiley that are very different from Waters, and the White House would benefit from making the distinction.

Such a distinction would allow the administration to engage a nation of black people that represent the left, independents, and moderate right who supported President Obama in 2008 at unprecedented numbers and now are frustrated for a multitude of reasons. But lets be clear, frustrated does not mean that they do not still support the President.

Even the drop in approval rating numbers for African-Americans (which has gone from 83 percent to 58 percent) can be misleading. Disapproval for many African-Americans means, “I still support you, I’m just not excited about you.” The supporters of neither the president, nor the president himself can afford to go into the campaign and convention mode with this demographic not only unengaged, but more importantly uninspired.

A meeting with Waters could send a message, but a real meeting, not a duty bound check them off list meeting, between the president with key black elected officials, faith leaders, business leaders, and others is what will solidify the base going into November.

Congresswoman Waters has ensured that the president is challenged, but to what end?

If the critique of the president further isolates him from even segments of a black electorate he needs to turn out more fervently than in 2008, it operates in contradiction to what many black leaders,Waters included, state they want; a second term.

However, the White House has the challenge of determining if they will erase the line in the sand as well, accept some of the critique of black disengagement as legitimate. Using this time as an opportunity to talk about what they have actually accomplished (which is substantial) while making some commitments to a community that will show up in November if the terms of the relationship are clear.

But this is less about policy and all about relationships — key relationships that won’t be repaired or solidified with any beverage of choice, but with truth serum.